Radiolabelling via fluorination of aziridines
An aziridine ring and labeling technology, applied in the field of positron emission tomography, can solve problems such as inapplicability
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[0406] Azeotropic drying in the presence of Kryptofix 222 (5 mg in 1.5 ml MeCN) and cesium carbonate (2.3 mg in 0.5 ml water) by heating at 100-120 °C for 20-30 min in a nitrogen stream 18 F-Fluoride (up to 40GBq). During this time, 3 x 1 ml MeCN was added and evaporated. After drying, the precursor solution (2 mg) in 150 μl DMSO was added. Seal the reactor, then heat in the range of 50-70°C for 5-15min to complete the labeling. The reaction was cooled to room temperature then diluted with water (2.7ml). The crude reaction mixture was analyzed by analytical HPLC. The expected by preparative radiation HPLC 18 F labeled peptide.
[0407] Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest potential. The following preferred specific embodiments should therefore be considered as illustrative only and not limiting in any way to the remainder of the disclosure.
[0408] All ...
Embodiment 1
[0439] Preparation of compounds of general chemical formula I and corresponding model compounds
[0440] Prepared according to Scheme 1 when n=0.
[0441] Preparation of methyl 1-trityl-ziridine-2-carboxylate 2a
[0442]
[0443] 3g (29.6mmol) of aziridine 1a was dissolved in 50ml of dichloromethane, cooled to 0°C, and then 6.17ml (44.51mmol) of triethylamine and 9.93g (35.61mmol) of trityl chloride were added. The mixture was stirred at room temperature for 2 h, then concentrated. The residue was purified by chromatography on silica gel to afford 9.96 g (98%) of 2a.
[0444] 1 H-NMR (CDCl 3 ): δ=7.41 (m, 6H), 7.30-7.17 (m, 9H), 3.77 (s, 3H), 2.26 (dd, 1H), 1.89 (dd, 1H), 1.42 (dd, 1H) ppm.
[0445] Preparation of 1-trityl-aziridine-2-carboxylic acid 3a
[0446]
[0447] 7.45 g (21.69 mmol) of 2a were dissolved in 55 ml THF, cooled to °C and then treated with 34.7 ml (34.71 mmol) 1N sodium hydroxide solution. The reaction mixture was stirred overnight at room temp...
Embodiment 2
[0533] Preparation of compounds of general chemical formula II and corresponding model compounds
[0534] When n=1, it is prepared according to route 2.
[0535] Preparation of (2-chlorosulfonyl-3,5-dimethoxy-phenyl)-acetic acid methyl ester 14a
[0536]
[0537] At -10°C, 0.4ml (6mmol) of chlorosulfonic acid was dissolved in 4ml of dichloromethane, followed by the slow addition of 600mg (2.85mmol) of (3,5-dimethoxy-2-methane) dissolved in 2ml of dichloromethane yl-phenyl)-acetic acid methyl ester 13a. The reaction mixture was stirred at room temperature for 1 h, diluted with 50 mL of ethyl acetate and washed with 10 mL of saturated sodium bicarbonate solution. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to afford 451 mg (51%) of crude 14a, which was used in the next step without further purification.
[0538] 1 H-NMR (CDCl 3 ): δ = 6....
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